Sodium Iodide → HCID 57747237, compound

HRID 1163459Notes

Reaction equation

HRID 1163459 reaction equation
[CH3:1][C:2]([C:6]1[CH:7]=[C:8]([C:18](=[O:21])[CH2:19]Br)[CH:9]=[C:10]([C:13]([CH3:17])([CH3:16])[CH2:14][CH3:15])[C:11]=1[OH:12])([CH3:5])[CH2:3][CH3:4].[I-:22].[Na+].CCCCCC>COCCOC>[CH3:1][C:2]([C:6]1[CH:7]=[C:8]([C:18](=[O:21])[CH2:19][I:22])[CH:9]=[C:10]([C:13]([CH3:17])([CH3:16])[CH2:14][CH3:15])[C:11]=1[OH:12])([CH3:5])[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8058HexaneHCID 86631892HCID 86631892, compound

Product 1

HCID 57747237HCID 57747237, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of 3.56 g (10 mmol) of 1-(3,5-bis(1,1-dimethylpropyl)-4-hydroxyphenyl)-2-bromo-ethanone in 15 ml of 1,2-dimethoxyethane, a solution of 1.65 g (11 mmol) of sodium iodide in 10 ml of 1,2-dimethoxyethane is added dropwise at room temperature. After the addition, stirring is continued for 16 hours at room temperature. Then 5 ml of hexane is added and, after stirring for additional 15 minutes, the precipitated salts are removed by filtration. The obtained solution is evaporated and the resulting residue is purified by recrystallization from hexane to give 2.15 g (53%) of compound 204, m.p. 76-77° C.

Workup

  1. additionAfter the addition
  2. stirringafter stirring for additional 15 minutes
  3. customthe precipitated salts are removed by filtration
  4. customThe obtained solution is evaporated
  5. customthe resulting residue is purified by recrystallization from hexane

Sources & evidence

ORD record
ord-e3c2295122d744929326802c3990d586
Source dataset
uspto-grants-2010_10
Patent number
US07820865B2

Reaction notes

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